


The Pen Is Mighter Than Blair's Sword

by DiscreetKitty



Category: Gossip Girl
Genre: Adult and Minor, Anal Sex, F/M, Het, Oral Sex, Vaginal Fingering
Language: English
Status: Completed
Published: 2016-10-18
Updated: 2016-10-18
Packaged: 2018-11-15 18:04:26
Rating: Explicit
Warnings: Underage
Chapters: 1
Words: 4,044
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/11236335
Author URL: https://archiveofourown.org/users/DiscreetKitty/pseuds/DiscreetKitty
Summary: Set in S2 E17. Flashbacks of sensual moments with Serena encourages Dan to have an intimate moment with Rachel in her office.





	The Pen Is Mighter Than Blair's Sword

**Author's Note:**

> I do not own Gossip Girl, nor the characters from it. I do not make any money from the writing of this story.

When Dan walked into Rachel's office, he wasn't surprised to see Rachel sitting near her bookshelf with her head in her hands. Dan knew she didn't realize he walked in. It wasn't liked he knocked on her door since it was already open. He normally would have announced himself before coming into the room. When he saw Ms. Carr sobbing on the floor, he knew that she wouldn't mind his unexpected visit.

"Rachel," he whispered as he slid on the floor next to her.

His back was pressed against a bulky dictionary. He moved in front of her, sitting on his knees so he could face her. She looked up at him, her swollen brown eyes pleading with him to say something. She swept her bang away from her face, brushing a strand of hair away from her sticky cheeks. She stopped flicking away her maple colored strands when Dan grabbed her hand.

"I can't believe this," she cried. "I never meant for any of this to happen."

"That's just what Blair does," Dan said.

His voice was low, slowly enunciating his words so Rachel would understand that the student - teacher sex scandal wasn't her fault. Blair was the one who started the rumor. She tried her hardest to prove to the Parent Committee, and mostly, to Mr. Waldorf, that she was telling the truth. If it wasn't for Blair, Rachel wouldn't be curling up against a wooden shelf, letting her tears trickle onto the plush white rug. Blair was the reason Rachel was fired from Constance.

"All because she didn't like a grade," Rachel said with a huff.

"That's Blair.

Dan noticed that Rachel was staring off at something for a minute. He hoped that she didn't see someone watching them. Although the two weren't doing anything wrong, it would look bad because of the rumors. Dan got up and closed the door. He sat back down in the same spot and noticed that she was still staring off. He looked around the room to try to figure out what she was looking at.

"The pen is mightier than the sword," Rachel randomly said."Isn't that true? Blair hurt me by writing an e-mail to Gossip Girl."

"That's Blair's superpower," Dan tried to joke but it didn't come off as funny. "She uses her pen as a sword."

Dan stopped talking when he noticed the way Rachel's chest moved up and down. Her breast rose and fell as her unsteady breath tried to find a gentle rhythm. Her v- neck long sleeved shirt drew more attention towards her bosom. The dark color of her shirt captured Dan's attention as her bust moved when she sobbed. She took a deep breath, trying to get in control of her emotions. It was clear to Dan that she was failing to regain control. She was upset and she deserved to be upset. Blair sabotaged her dream of teaching in the Big Apple. How could anyone easily get over that?

"And Serena?" she asked.

Dan assumed that she was referring to the last thing he had said. His mind raced as he tried to remember the words that came out of his mouth. He had been so memorized by Rachel's chest that he forgot what he had said. He noticed that Rachel was staring at him and he must have looked confused to her.

"Why would Serena do this?" Rachel asked as a tear escaped from her eye. "She was a friend. I didn't do anything to her."

"She was jealous," Dan said, mostly to himself.

Honestly, he wasn't even sure why Serena decided to frame Rachel. Serena actually caused more damage than the 95 pound, doe-eyed, bon mot tossing, label whoring package of girly evil. His beautiful blond dream girl took a picture of Rachel and him hugging. Then, she presented the photo to the Parent Committee as evidence of a sexual relationship. Dan couldn't believe that someone as radiant and sexy as Serena would feel jealous of the small town beauty.

"Why?" she asked.

Dan was still holding her hand when she scooted closer to him. He looked down at her tan hand and noticed how small and fragile it was. He looked into Ms. Carr eyes, realizing that she was too naive and too vulnerable to live in New York. He knew she felt like a small fish in a big pond. She was too gung-ho to understand that she didn't belong in Manhattan. She was like him. The outsider that had a front row seat into the scandalous world of the insiders. Unlike Dan, she didn't have the guile to withstand the fiery darts of the rich. She was weak and she needed someone to protect her. She needed Dan.

"Why," he repeated. He was making a statement rather than asking a question. "You have what she doesn't."

Rachel arched her eyebrow.

"You know what that is?" he asked her, feeling her hand soften in his grip.

"What is that?" she asked.

"Serena always told me that she was afraid that no one saw the real her," he began. "In reality, she was the only one who didn't know the real Serena. That's why she's jealous. You know who you are and you're not afraid to take a stand for it."

Dan sighed as he released Rachel's hand from his grip. He ran a hand through his curly dark hair.

"You and Serena," Rachel began. "Are you guys okay?"

He shook his head, then threw his head back and covered his eyes with his hands.

"That bad?" she asked.

"We're done," he said as he lowered her head. "It was a mutual decision. She used the photo of us to hurt me. Blame me for bringing you down."

The next thing Dan knew was that there were two hands on his face. Rachel had stood up on her knees, cupping her face to comfort him. He was staring directly into her eyes. He could smell her favorite mint candy from her breath. He felt the pulse from her thumb on his face. It was like her heart was beating for him. He broke eye contact and looked down at her slender neck. He felt an urge to reach over and place his lips on her soft flesh. Maybe Blair and Serena knew something he didn't. Maybe he did have a thing for Constance's newest English teacher.

"It's not your fault!" she cried. "You have been nothing but good to me. Serena is terrible for what she did to you. Her best friend is Blair. Of course, she wouldn't appreciate the nicest boy at St. Jude."

"That's the Upper East side for you," Dan commented.

He stopped talking when Ms. Carr pulled his face closer to hers. Dan noticed that her eyes were staring at his lips. Her chest was heaving again and he could feel her heart beating faster from the pulse in her thumb. She lowered her voice an octave.

"You deserve so much Daniel Humphrey,"she whispered. As Dan leaned into her embrace, she repeated the words "so much."

Dan's brain shut down and pure lust took over. Every single decision was driven by the desire to pick the skinny teacher off the floor and throw her onto her desk. He imagined himself pulling off her black dress slacks, throwing her black lace panties onto the doorknob and pumping his length into her tight center. He could hear her moans in his head and smell her arousal just from thinking about it. The thought of taking the Iowan native made his member harden in his L.L. Bean jeans.

Dan's thoughts snapped back into reality when Ms. Carr sucked his bottom lip. He was surprised that Rachel didn't start the kiss by pressing her lips into his or kissing his chin. The kiss told Dan that Rachel didn't just want to make - out. She wanted to be fucked. She wanted to pull her top off and smothered the poor high schooler with her knockers. She wanted to be on all fours with Dan jackhammering into her small frame. She wanted to take the little high schooler and make him her man.

And Dan had no problem complying to that.

When he kissed back, Rachel immediately made the kiss rougher. She bit his lip and began swirling her tongue into his mouth. He tried poking his tongue into her but the teacher didn't allow her student to take over. She was in control and Dan was becoming too intoxicated from the kiss to usurp her dominance. She placed a gentle hand on his shoulder, only to push him down onto the ground. She fell on top of him without removing her tongue from his mouth. Her nipples were poking through the fabric of her thin purple shirt. Dan could feel her nubs harden against his chest.

Dan tried to picture what it would look like if the headmistress walked in now. His head was lying on the edge of Rachel's rug. Rachel's hair was dangling in his face. Her hands were pressed against his shoulders. His arms were grabbing the hips of the woman that was straddling his torso. His back was pressed against the softness of the thickly stranded mat. Ms. Carr's knees were placed on both sides of his hips, which meant that her ass was sticking up in the air. His legs were spread and his ankles were hanging off the side of the carpet, lying on the hard wooden floor. Dan knew that the headmistress would call the cops if she found the forbidden couple frolicking.

He considered telling the Iowan native to stop. There was too much at stake to fornicate in Rachel's office.

What would Yale think if they knew that the aspiring writer from Brooklyn was knocking ankles loose with an English teacher? The New Haven university would suspect that St. Jude's lonely boy sexed teachers up for good grades. Even if Yale overlooked the sex scandal, he'll be the laughing stock of the university. He imagined being labelled with the nickname, Handsome Dan, which was the name of the university's mascot. Everyone would see him as a dog, a no-good sex crazy animal.

Dan thought about how angry his father would be if he knew what Dan was doing. Rufus would assume that Dan had lied to him when the curly haired Humphrey assured his father that the student- teacher sex rumor was false. It was already enough that the ex-musician had to deal with Jenny dropping out of school and running away. Jenny was a handful by herself. Dan didn't need to add any more problems to his dad's plate.

There would be serious consequences for Rachel if they were caught in the act. She would be banned from teaching, put in prison and have to register as a sex offender. Rachel wouldn't be able to handle that.

"This isn't a good idea," Dan said.

Dan thought she understood that he wanted to stop when she sat up. The teacher raised her top over her lacy black bra and tossed the purple fabric behind her. Dan was about to explain to the recently fired faculty member why they shouldn't consummate the relationship in school. He wasn't going to let his arousal for the Heartland native force him to forgo his morals. He wasn't a sex-crazed monster like Chuck or a "desperate for some womanly affection" addict like Nate. He was better than Bass and Archibald. He was ...

Rachel looked lustfully into Dan's eyes when she reached down to squeeze Dan's growing member. Lust once again took over his brain and he let go of his inhibitions. He forgot the reason why he wanted to deny Ms. Carr from getting lucky when she began palming the bulge in his pants.

As her hands caressed his aching member, he grazed his fingers on the exposed skin of her breast. He raised his head and his shoulders when he reached around Rachel to unclip her bra. The movement was so swift that he made Rachel gasp. With his head still elevated off the rug, he captured one of Rachel's nipples with his mouth. He used his teeth to lightly graze the light brown nub. He grabbed her shoulder to steady himself as he suckled her. He looked up at the beauty above him and noticed she was biting her lip. He licked the top of her nipple before biting on the hard little nub. He switched breast when Rachel began moaning.

Dan stopped lavishing his teacher's tits when she started adding more pressure to his dick. His head fell back onto the rug and he placed his hands on his forehead. He closed his eyes when he felt a small pair of hands undo his leather belt. He could barely feel Rachel's touch when she unbuttoned his jeans and tugged down his metal zipper. He quickly sat to remove his shirt when Rachel lowered herself to pull off his shoes. She crawled back up to the high schooler to give him a quick peck. Dan let Rachel pull off the remainder of his clothes.

Rachel seemed to eager to go down on her student. Dan was surprised that she immediately engulfed him whole and began playing with his balls. Whenever Serena blew him, she always licked his head first before deep - throating him. The thought of his pretty blond ex - girlfriend reaching into his jeans, pulling out his half inflated member and licking up his pre-cum made him moan. He missed the way Serena would kiss his balls while pumping his length. He loved the way Serena would swallow his cum and then suck him dry so she could taste more of his delicious seed.

Dan stopped thinking about Serena when Rachel took his member out of her mouth. Dan groaned as Rachel began sucking him harder. As he watched the small town honey envelop his cock, he thought about how Serena would create such a wonderful feeling of friction with her teeth and tongue. He moaned as he thought about the time Serena blew him at the beach during the white party. He had missed her over the summer and needed to be with her again. He wouldn't have had sex on the beach if it wasn't for Serena. The two had made out for hours and the next thing Dan knew, she unzipped his pants and began licking his head. He remembered the way her blue eyes looked up at him as she took him farther into his mouth. The lust in her eyes made Dan forget that they were on the beach. The two had sex in the sand for so long that Dan's dick was coated with Serena's juices, spit, and sand. It was uncomfortable riding the bus home with sand all over his groin but it was worth it.

The thought of Serena made him feel like he was about to cum. He felt his ball tightened right before his cock spewed out white liquid down Rachel's throat.

As Rachel swallowed his sperm, Dan noticed that Rachel's face looked like she was ready to devour him. She took him out of her mouth and got right on top of her victim. Before she could do anything, Dan flipped Rachel over and yanked off both her slacks and her black lacy panties.

Dan stood up and Rachel walked over to her desk. She gripped the edge of the wooden surface and raised her ass in the air. She spread her legs and gave Dan a great view of her dripping hairless cunt. He positioned himself to enter her but stopped when he thought about Serena. The two had just broken up and he was using Rachel to rebound on Serena.

Rachel must have sensed his hesitation because she turned her head around and whispered,"It's okay Dan. We already got in trouble for having sex so we mind as we'll do it."

Dan began wondering if that was the only reason the two were having sex. He thought about how Nate felt about keeping his love for the Lord's mother secret. Nate and Catherine Beaton's relationship was never meant to last. Nate's heart was broken in the process and Catherine suffered serious consequences. Of course, Nate was having sex in exchange for Catherine's money, but he still seemed like he liked her. Dan didn't want that type of drama in his life. He knew that was exactly what would happen if he slept with Rachel. It wasn't too late to stop this.

"This still isn't right," Dan said.

"You're right," she whispered. She started swaying her hips back and forth. "But I want this."

"Ms. Carr -"

"Please, Dan. Please, please fuck me."

Rachel turned around and sat on her desk. She cupped Dan's face and pulled him closer to her. She looked so vulnerable and so needy. Dan knew that he shouldn't do this but his arousal was starting to get the better of him. Dan allowed Rachel to take his hands and place them on her breast. He kissed her soft mounds again, nibbling the hardened flesh. He looked up at Rachel when she covered her mouth to muffle her scream. Dan grabbed her face to kiss again but Rachel pushed him back.

He was confused for a second until he noticed that Rachel spread her legs. Dan watched as Rachel slid her middle finger between her lips. Dan was memorized when Rachel brushed her thumb over her swollen clit. She slid two fingers into herself, moaning as her the scent of her arousal filled the room. Her glistening pink flesh looked so inviting that Dan grabbed her by the knees, lifted her thighs up and stepped between her slender legs.

He slid into her with such ease that Dan knew that this wasn't just about revenge. This wasn't Rachel using Dan to get back at the school for firing her over a rumor. It was obvious that Rachel really liked him. As he slowly thrust back and forth, he was relieved that it didn't feel wrong. He had to admit it. He liked Rachel and having sex with her felt right. Every single sensation that he was experiencing felt right. The way his cock was surrounded by a tight, damp warmth felt right. The way Rachel's damp warmth sent shivers through his balls and spine felt right. The way she smiled at him when he pushed himself deeper into her felt right.

Dan knew that Rachel wanted more by the way she grabbed him by the waist, pulling him into her with each thrust. He lifted her legs on his shoulders so he could grip the front of her upper thighs. She clenched around his member as he pushed faster into her. He pumped into her, the room was filled with the combination of his grunts and her moans. Dan stared at Ms. Carr as her lips parted to let quick, hitching breaths escape. Dan knew that Rachel was getting ready to orgasm. He plunged into her with greater speed, making Rachel cry loudly. He placed a hand over her mouth to muffle the sound.

As her body went limp, Dan could feel his own orgasm approaching. He wasn't sure if Rachel wanted him to pull out. He decided it was better to ask than assume.

"I'm about to cum," he warned. "You want me to pull-"

"Yes," she whispered. She was still recovering from her climax.

Dan gently pulled out, feeling afraid that any sudden movement would make him erupt. Before he could think about what to do next, Rachel turned over and pointed to her round little butt. Dan assumed that Rachel was too out of breath to speak so body language was the only way she could communicate. Dan fully understood what Rachel wanted. He spread her cheeks and pushed into her unlubricated backside. He wanted to hold off his orgasm as long as possible. The last thing he wanted to do was go limp. Some of his fluids seeped into her, soaking up her dried back side.

Rachel's back entrance was a lot tighter than Serena's. As he pushed into Rachel, he thought about the last time he and Serena had anal sex. It happened before they had gotten back together. Dan tried to place the date but all he remembered it was before Chuck's dad's funeral. He remembered that the conversation had somehow ended with the two agreeing that the first time they had sex was the greatest night of both of their lives. Everything had happened so fast that the next thing Dan knew was that Serena was down on all fours in front of him. He remembered feeling strange. Serena made it clear she didn't want to resume the relationship but she needed him. She had just broken up the polyamorous photographer, Aaron, and she needed to feel loved.

He remembered seeing the raw lust in Serena's eyes as she pulled apart her ass cheeks. He had spit right on the puckered hole and lined his dick up.

"Keep it slow, Dan," he remembering Serena saying in a sultry voice. She giggled before saying "I haven't been buttfucked in a while."

She was tighter than he had expected her to be. He pushed slowly into her, making her moan in the process.

"I can feel your cock stretching my asshole out," he remembering her saying. "You're cock is so big. Fuck, that feels so good."

Serena loved talking dirty. She never held back exactly what she was feeling or what she wanted. He loved how she was in charge of her sexuality and she never felt ashamed to express desire.

Dan realized that Rachel only moaned during sex. She wasn't talking dirty or even saying if she liked something. This meant that Dan would have to assume what she liked. Dan hadn't been with a woman that made him had to read her mind in bed. It wasn't like he had been with a lot of girls before. Rachel was actually the third person he had sex with. The first girl was a bubbly blond that he had met at a summer camp from young authors. She wasn't a virgin and she had no problem telling him what to do.

He stopped thinking about his past sexual experiences as Rachel pushed back against him. He couldn't hold off any longer and exploded inside of her. He went limp as his semen dripped out of her rear end. He pulled out of her and sat on the desk. She stood up and Dan noticed that her entire body was covered in chill bumps. Still, she walked over to him, cupped his face and gave his a huge kiss. The two kiss for a few seconds until Rachel pulled away.

"Are you okay?" she asked as she put her black bra back on.

"I'm great," he said with a smirk.

Rachel smiled the second she noticed the smirk. She slipped her shirt over her freezing torso and quickly pulled her dress slacks over shivering legs. She handed Dan his shirt and boxers.

"I like you, Rachel," Dan said as he stood up to put his boxers back on.

Rachel's eyes lit up as she put her shoes back on.

"I do, too," she whispered.

Dan finally noticed the Edward Bulwer-Lytton quote taped on the wall.

"The pen is mightier than the sword," Dan read. "So that's what you were looking at earlier."

Rachel nodded as she handed him his pants.

"You know," Rachel began as she stared down as Dan's crotch. "In Twain's The Adventure of Tom Sawyer, there's a picture of the quote on the school board. The words "pen" and "is" are too close together. It read 'the penis mightier than the sword."

"If the penis is mightier than the sword, that means sex resolves more than communication does," Dan said. He didn't grasp the significance of his statement until Rachel kissed him.

"I agree," she giggled. "Blair's pen stabbed me deeper than a sword but your penis made me feel better."

"Please don't talk about Blair and my penis in the same sentence."

The two chuckled before engaging in one last kiss.

**Author's Note:**

> Thank you for reading my Gossip Girl fic. Please favorite and/or review! Follow me at tumblr at DiscreetKitty and @DiscreetKity96 on Twitter for updates on stories and post about fandoms.


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